The stories span industries from technology to real estate. Market miscalculations, short-term thinking and rotten ethics are the broad themes. Taken together, the collective devastation of these miscues in current dollar value creeps into the trillions.

To be fair, some of these blunders were more unforeseen--and the blunderers more naturally disadvantaged--than others.

Take the Canarsee natives, who, in 1626, traded for trinkets a now rather stylish plot: Manhattan (then called New Amsterdam). The island fondly dubbed "the center of the universe" by many New Yorkers is now worth a cool $1 trillion, estimates Matthew Mondanile of Cushman & Wakefield, a global commercial real estate firm.

In another short-sighted deal, the Dutch later traded New Amsterdam to Great Britain in exchange for what is now the Republic of Suriname, a small country in South America with a wee gross domestic product of $2.9 billion.

Napoleon probably had more financial foresight than the Canarsees, but maybe not much. Back in 1803, the diminutive emperor was struggling to defend France's New World conquests, including Haiti, which was then in the midst of a slave revolt. Stretched thin but not willing to relinquish the island, Napoleon offered to sell the entire Louisiana Territory, rather than just the port of New Orleans, as had previously been discussed.

His offer: $15 million--3 cents per acre--or about $284 million today. The current value of that land, which now includes portions of 15 U.S. states and two Canadian provinces: about $750 billion, figures Mondanile. And Haiti? Less than a year after France inked the sale, Haiti won its independence.

OK, so it's hard to make objective decisions in the heat of battle. But what about when times are good and opportunities aplenty?

In the mid-1950s, Ford Motor, flush from its exceptionally successful Thunderbird, wanted to create a new model to compete head-to-head with General Motors' Oldsmobile. (The Ford Lincoln had served that purpose, but it was getting a makeover to go against GM's higher-end Cadillac.) Ford's solution: the Edsel, named after the son of founder Henry Ford.

Despite all the hype--including a television special called The Edsel Show--the Edsel proved to be one of the biggest bungles ever in the auto industry. Ford whiffed on three fronts: style (the car looked too much like other Ford models), size (too large, given the growing trend toward compact cars), and price (initially intended to be priced between a Lincoln and the lower-tier Mercury, the Edsel actually fell within Mercury's price point, and thus confused consumers). Ford sank $350 million (in 1950s dollars) into the Edsel before calling it quits; production of the model ceased Nov. 19, 1959.